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Place crescent roll cans in the freezer for about 30 minutes.
Preheat the oven to 350 degrees Fahrenheit and line baking sheets with silicon mats or parchment paper.
Beat cream cheese, vanilla and sugar with an electric mixer until smooth and fluffy.
Open the cans and slice each into 12 pieces, approximately ½″ slices. (Don’t unroll them, pretend they’re slice and bake cookies.)
Place six slices on a cookie sheet, flattening the centers to create an indent. (I used a large spice container dipped in flour, plus my fingers for a little extra flattening in the middle.)
Fill the indent half with the cream cheese mixture and half with the pie filling.
Bake until edges are golden brown, about 15 minutes.
Cool completely on a wire rack.
In a small bowl, mix a large spoonful of powdered sugar with a little milk until liquid but still thick. Spoon into a pastry bag or Ziploc, cut off the tip, and drizzle over the pastries.